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The preliminary sketches for 'Sienese Landscape' were executed during the Easter of 1959. Weight had spent a week with the artist Leonard Rosoman at the Villa Solario, Malatrasca, which is situated about four miles outside Siena. Weight painted the landscape periodically between 1959 and 1963. 'Sienese Landscape' was originally larger than its present dimensions. Weight reduced the canvas size and redesigned the image in 1963.

Sienese Landscape resulted from Carel Weight's visit to Tuscany with his friend and colleague Leonard Rosoman, when they were in charge of students from the Royal College. Soon after it was acquired by the Tate Gallery, he wrote (11 Sept. 1963):

The preliminary sketches were done four years ago at Easter time. I spent a week with Leonard Rosoman at the Villa Solario, Malatrasca which is about four miles outside Siena. I painted this landscape on and off during the last three years. Originally it was rather larger and never quite seemed to work. Eventually, earlier this year, I reduced the size and redesigned it into its present state. I have a small oil sketch on which the idea of the picture evolved.

One result of this reduction in size is that the paint overlaps and has cracked along the edges where the canvas has been turned over a smaller stretcher; the strips turned over on all four sides are c.40-45 mm (1 1/2-1 3/4 in) wide. Cutting down has been a relatively common solution for Weight although he admitted that he remained dissatisfied with this painting (conversation with the author, 8 Dec. 1995). As with many of his works, there is a mixture of impasto and scraping in the application, and the bare canvas is visible in parts of the tree to the left. A wistful atmosphere lingers in the movement of the trees and clouds, and the labouring woman. In discussing the work with Cathy Courtney ('Artists' Lives', National Life Story Collection, British Library National Sound Archive, 1991, Tate Gallery Archive, tape F2550 side B), Weight commented that it was difficult to adjust to a new country over a short period. A larger work by the same title was exhibited in Weight's Ghosts, Marvels, Moments and Scenes from Foreign Lands show at Zwemmer's Gallery (1960).